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For example:

It happened only a handful of times in my lifetime: once when I went to the store. It just had to be done. There was no choice. Another when heading to the beach in 2013...

Should I just leave out the colon and use a period instead?

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How is "only a handful of times" followed by once? Is that an example occurrence? –  Andrew Leach Apr 29 '13 at 14:57
    
In which case 'One of these was ...' seems a less non-standard way to continue after the period option. –  Edwin Ashworth Apr 29 '13 at 15:09
    
I would use an em dash instead of a colon in the opening sentence, to indicate the fairly strong yet attenuated connection between the "once" clause and the preceding portion of the sentence: "It happened only a handful of times in my lifetime—once when I went to the store." The subsequent sentences can stand as written, although the sentence beginning "Another..." might benefit from your adding a noun after "Another" to reinforce its connection to the "handful of times." For example, "Another instance occurred when I was heading to the beach..." Ultimately, this is copyediting advice. –  Sven Yargs Apr 29 '13 at 22:18
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3 Answers

When a colon introduces more than one sentence, capitalize all of the sentences. For example:

To get rich quick: Invent a time machine. Use the machine for day trading. Beware of future versions of yourself (and other stalkers). Profit.

Some style guides (for example, AP but not Chicago) recommend capitalizing any complete sentence that follows a colon.

In your example, capitalizing “Once, when I went to the store” would clarify that you intend it as an (incomplete) sentence.

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If the "once" is an example, it should be introduced with a comma rather than a colon. If you want to list all the cases, a colon would be legitimate, e.g., "It happened only a handful of times in my lifetime: once when I went to the store, once when I was conga dancing, and once when I was watching Plan 9 from Outer Space." "Once when I went to the store" is a subordinate clause, not a sentence, so the whole thing is one sentence.

The sentences following "to the store" aren't relevant. You aren't setting up a series of occurrences with them.

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My question is what to do when one of your items needs further explanation. A parentheses would do I guess. –  Absolute0 Apr 29 '13 at 15:49
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This reads like fiction, and so you have more creative license. I would word the passage like this to capture the list and the parenthetical within the list.

It happened only a handful of times in my lifetime: The first time, when I went to the store--it just had to be done; there was no choice--another time when heading to the beach in 2013...

I would use the em dash instead of parentheses to keep with the informal tone. Per The Elements of Style:

"A dash is a mark of separation stronger than a comma, less formal than a colon, and more relaxed than parentheses."

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I like this solution best, but it won't work if the part following the em dash has multiple sentences. –  Absolute0 Jun 13 '13 at 10:53
    
Not true. You can include multiple sentences inside em dashes. –  tylerharms Jun 13 '13 at 13:10
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